EP0127114A1 - Process for the cleavage of phthalimides - Google Patents

Process for the cleavage of phthalimides Download PDF

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EP0127114A1
EP0127114A1 EP84105830A EP84105830A EP0127114A1 EP 0127114 A1 EP0127114 A1 EP 0127114A1 EP 84105830 A EP84105830 A EP 84105830A EP 84105830 A EP84105830 A EP 84105830A EP 0127114 A1 EP0127114 A1 EP 0127114A1
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cleavage
formula
amino
phthalimides
och
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EP0127114B1 (en
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Helmut Dr. Hagen
Rolf-Dieter Dr. Kohler
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1. A process for the cleavage of a phthalimide of the formula I see diagramm : EP0127114,P4,F2 where R is an optionally substituted aryl or hetaryl, wherein a compound of the formula I is treated with an alkanolamine.

Description

Die Erfindung betrifft ein Verfahren zur Spaltung von Phthalimiden der Formel I

Figure imgb0001
in der

  • R ein Substituent ist und der Ring A noch substituiert sein kann, das dadurch gekennzeichnet ist, daß man die Verbindungen der Formel I mit Alkanolaminen behandelt.
The invention relates to a process for the cleavage of phthalimides of the formula I.
Figure imgb0001
 in the
  • R is a substituent and the ring A can still be substituted, which is characterized in that the compounds of the formula I are treated with alkanolamines.

Die Reste R können aliphatische, cycloaliphatische, aromatische oder heterocyclische Gruppen sein.The radicals R can be aliphatic, cycloaliphatic, aromatic or heterocyclic groups.

Es kommen z.B. gegebenenfalls durch Alkoxy, Cyan, Carbonamid, gegebenenfalls substituiertes Amino oder Aryl substituiertes Alkyl, Cycloalkyl, gegebenenfalls durch Halogen, Nitro, Alkyl, Alkoxy, Cyan, Carbamoyl, Formyl, Sulfamoyl, Cyanmethyl, Alkoximethyl, Aryloximethyl, Arylthiomethyl, Arylsulfonylmethyl, Aryl, Benzoyl, Vinylaryl, Vinylimidazolyl oder Carboxyl substituiertes Aryl, gesättigte und ungesättigte Heterocyclen oder auch Alkenyl in Betracht.For example, alkyl, cycloalkyl optionally substituted by alkoxy, cyan, carbonamide, optionally substituted amino or aryl, optionally substituted by halogen, nitro, alkyl, alkoxy, cyan, carbamoyl, formyl, sulfamoyl, cyanomethyl, alkoximethyl, aryloximethyl, arylthiomethyl, arylsulfonylmethyl, aryl, benzoyl, Vinylaryl, vinylimidazolyl or carboxyl substituted aryl, saturated and unsaturated heterocycles or alkenyl are also suitable.

Einzelne Reste R sind z.B.:

  • CH3, C2H5, C3H7, C4H9, C5H11, C6H13, C7H15, C8H17, C10H21, C12H25, C2H4OCH3, C2H40C4H9, C4H8OCH3, (CN2)5CN, C2H4N(CH3)2, C6H4Cl, C6H4NO2, C6H4CH3, C6H4OCH3, C6H3Cl2, C6H3(N02)2, C6H4CN, C6H4COOH, C6H4CONH2, C6H4CHO, C6 H 4 S02 C 6H5, C6H4 CH2CN, C6H4OCH3, C6N4CH2OCH3, C6H4CH2SCH3, C6H4CH2SC6H5, C6H4CH2SO2C6H5, C6H5, C6H4COC6H5 oder C2H4C6H5.
Individual residues R are, for example:
  • CH 3 , C 2 H 5 , C 3 H 7 , C 4 H 9 , C 5 H 11 , C 6 H 13 , C 7 H 15 , C 8 H 17 , C 10 H 21 , C 12 H 25 , C 2 H 4 OCH 3 , C 2 H 4 0C 4 H 9 , C 4 H 8 OCH 3 , (CN 2 ) 5 CN, C 2 H 4 N (CH 3 ) 2 , C 6 H 4 Cl, C 6 H 4 NO 2 , C 6 H 4 CH 3 , C 6 H 4 OCH 3 , C 6 H 3 Cl 2 , C 6 H 3 (N0 2 ) 2 , C 6 H 4 CN, C 6 H 4 COOH, C 6 H 4 CONH 2 , C 6 H 4 CHO, C 6 H 4 S 0 2 C 6 H 5 , C 6 H 4 C H 2 CN, C 6 H 4 OCH 3 , C 6 N 4 CH 2 OCH 3 , C 6 H 4 CH 2 SCH 3 , C 6 H 4 CH 2 SC 6 H 5 , C 6 H 4 CH 2 SO 2 C 6 H 5 , C 6 H 5 , C 6 H 4 COC 6 H 5 or C 2 H 4 C 6 H 5 .

Der Ring A kann beispielsweise noch durch Chlor, Brom, Nitro, Carboxy, Carbamoyl oder Sulfamoyl substituiert sein.The ring A can also be substituted, for example, by chlorine, bromine, nitro, carboxy, carbamoyl or sulfamoyl.

Die Verbindungen der Formel I können nach an sich bekannten Methoden hergestellt werden, beispielsweise durch Umsetzung einer Halogenverbindung mit Phthalimidkalium nach Gabriel.The compounds of formula I can be prepared by methods known per se, for example by reacting a halogen compound with phthalimide potassium according to Gabriel.

Die Spaltung der Phthalimide zu den Aminen und Phthalsäuren oder Derivaten davon stößt in der Praxis häufig auf große Schwierigkeiten. Die saure Hydrolyse mit 20 bis 30 %iger Salzsäure erfordert meist langes Erhitzen Bg/uw unter Rückfluß (Liebig Ann. chem. 1949, 22) oder Temperaturen von 200°C unter Druck (Chem. Ber. 20, 2224 (1887)). Die alkalische Hydrolyse mit wäßrigen Laugen bleibt im allgemeinen auf der Stufe der Phthaliminsäuren stehen. Zur vollständigen Hydrolyse muß eine Behandlung mit Mineralsäuren nachgeschaltet werden (Chem. Ber. 37, 1038 (1904)). Die Spaltung der Phthalimide der Formel I mittels Hydrazin bereitet im Labormaßstab zwar kaum Probleme, in technischen Dimensionen erwachsen jedoch große Schwierigkeiten. Das bei der Reaktion entstehende schwerlösliche Salz des cyclischen Phthalsäurehydrazids (Nature (London) 158, 514 (1946)) fällt als voluminöser Niederschlag aus, so daß zur Handhabung große Mengen an Lösungsmitteln und große Reaktionskessel benötigt werden. Die akute Toxizität und der hohe Preis von Hydrazin stehen einer wirtschaftlichen Anwendung ebenfalls hinderlich im Weg.The cleavage of the phthalimides to the amines and phthalic acids or derivatives thereof often encounters great difficulties in practice. The acidic hydrolysis with 20 to 30% hydrochloric acid usually requires long heating Bg / uw under reflux (Liebig Ann. chem. 1949, 22) or temperatures of 200 ° C under pressure (Chem. Ber. 20, 2224 (1887)). Alkaline hydrolysis with aqueous alkalis generally remains at the phthalimic acid level. For complete hydrolysis, treatment with mineral acids must be followed (Chem. Ber. 37, 1038 (1904)). The cleavage of the phthalimides of the formula I by means of hydrazine hardly poses any problems on a laboratory scale, but great difficulties arise in technical dimensions. The sparingly soluble salt of the cyclic phthalic hydrazide (Nature (London) 158, 514 (1946)) formed during the reaction precipitates out as a voluminous precipitate, so that large amounts of solvents and large reaction vessels are required for handling. The acute toxicity and high price of hydrazine are also an obstacle to economical use.

Es war deshalb außerordentlich überraschend, daß es erfindungsgemäß leicht gelingt, Phthalimide zu spalten.It was therefore extremely surprising that phthalimides can easily be cleaved according to the invention.

Die Spaltung der Phthalimide der Formel I geschieht durch einfaches Erwärmen der Verbindungen in Alkanolaminen. Diese fungieren sowohl als Lösungsmittel wie auch als Reaktionskomponenten. Als Alkanolamine geeignet sind z.B. Monoethanolamin, Monoisopropanolamin, 3-Aminopropanol oder Aminoethylethanolamin. Vorzugsweise findet Monoethanolamin Verwendung. Die Reaktionstemperaturen liegen in einem Bereich von 40 bis 140°C, vorzugsweise bei 60 bis 100°C. Die Aufarbeitung der Reaktionsmischung hängt von der Natur des freigesetzten Amins ab und ist in der Regel sehr einfach. Beispielsweise kann man wasserunlösliche, feste Amine normalerweise durch Zugabe von Wasser abscheiden. Wasserlösliche Amine können durch Extraktion mit einem Lösungsmittel wie Methylenchlorid, Essigester oder Toluol isoliert werden. Die bei den Umsetzungen freigesetzten Alkanolamide der Phthalsäure verbleiben in der wäßrigen Phase und können deshalb problemlos abgetrennt werden.The phthalimides of the formula I are cleaved by simply heating the compounds in alkanolamines. These act both as solvents and as reaction components. Suitable alkanolamines are e.g. Monoethanolamine, monoisopropanolamine, 3-aminopropanol or aminoethylethanolamine. Monoethanolamine is preferably used. The reaction temperatures are in a range from 40 to 140 ° C., preferably from 60 to 100 ° C. Working up the reaction mixture depends on the nature of the amine liberated and is generally very simple. For example, water-insoluble solid amines can usually be separated by adding water. Water-soluble amines can be isolated by extraction with a solvent such as methylene chloride, ethyl acetate or toluene. The alkanolamides of phthalic acid released during the reactions remain in the aqueous phase and can therefore be removed without problems.

Man kann natürlich die Spaltung auch in Gegenwart zusätzlicher Lösungsmittel vornehmen, insbesondere, wenn die Spaltprodukte mit den Alkanolaminen reagieren können und somit ein Uberschuß Alkanolamin über die stöchiometrisch erforderliche Menge hinaus unzweckmäßig ist. Zum Beispiel empfiehlt es sich in Gegenwart austauschbarer Halogenatome nur mit ungefähr stöchiometrischen Mengen an Alkanolaminen zu arbeiten.The cleavage can of course also be carried out in the presence of additional solvents, in particular if the cleavage products can react with the alkanolamines and an excess of alkanolamine beyond the stoichiometrically required amount is therefore unsuitable. For example, in the presence of interchangeable halogen atoms, it is advisable to work only with approximately stoichiometric amounts of alkanolamines.

Bei der Spaltung verwendbare Lösungsmittel sind beispielsweise Alkanole, Glykole, Glykolether, Ketone, Halogenkohlenwasserstoffe oder Kohlenwasserstoffe. Im einzelnen seien z.B. Methanol, Ethanol, Propanol, Butanol, Glykol, Methyl- oder Ethylglykol, Aceton, Methylethylketon, Tetrahydrofuran, Dioxan, Methylenchlorid, Chlorbenzol oder Toluol genannt.Solvents which can be used in the cleavage are, for example, alkanols, glycols, glycol ethers, ketones, halogenated hydrocarbons or hydrocarbons. In particular, for example Methanol, ethanol, propanol, butanol, glycol, methyl or ethyl glycol, acetone, methyl ethyl ketone, tetrahydrofuran, dioxane, methylene chloride, chlorobenzene or toluene.

Der Phthalimidrest dient in der Regel als Schutzgruppe, d.h. seine Anwesenheit ermöglicht Reaktionen, die in Gegenwart einer freien Aminogruppe nicht möglich sind. Beispielsweise können bei geschützter Aminogruppe Alkylierungen, Acylierungen, Nitrierung, Halogenierungen, Chlorsulfonierungen oder Oxidationen vorgenommen werden.The phthalimide residue usually serves as a protective group, i.e. its presence enables reactions which are not possible in the presence of a free amino group. For example, alkylations, acylations, nitration, halogenations, chlorosulfonations or oxidations can be carried out in the case of a protected amino group.

Besonders wertvoll ist das neue Verfahren für Verbindungen mit aromatischen oder heteroaromatischen Resten R, insbesondere Phenyl-, Naphthyl-, Thiazolyl-, Thiadiazolyl-, Imidazolyl-, Benzthiazolyl-, Benzimidazolyl-, Indolyl-, Pyridyl- oder Chinolinylresten.The new process is particularly valuable for compounds with aromatic or heteroaromatic radicals R, in particular phenyl, naphthyl, thiazolyl, thiadiazolyl, imidazolyl, benzthiazolyl, benzimidazolyl, indolyl, pyridyl or quinolinyl radicals.

Beispiel 1example 1 2-Amino-benzylcyanid2-amino-benzyl cyanide

100 g 2-Cyanomethyl-N-phenyl-phthalimid wurden bei 80°C portionsweise in 100 g Monoethanolamin eingebracht. Nach 10 Minuten wurde auf 20°C gekühlt und 400 g Eiswasser wurden zugetropft. Das ausgefallene Produkt wurde abgesaugt und mit Eiswasser neutral gewaschen. Ausbeute: 40 g (80 % d. Th.) Fp. 70°C100 g of 2-cyanomethyl-N-phenyl phthalimide were introduced in portions into 100 g of monoethanolamine at 80 ° C. After 10 minutes, the mixture was cooled to 20 ° C. and 400 g of ice water were added dropwise. The precipitated product was filtered off and washed neutral with ice water. Yield: 40 g (80% of theory), mp. 70 ° C.

Beispiel 2Example 2 1-(2-Aminobenzyl)-imidaxol1- (2-aminobenzyl) imidaxol

30 g 2-(1-Imidazolylmethyl)-N-phenyl-phthalimid wurden in 60 g Monoethanolamin 1 Stunde bei 70°C gerührt. Nach dem Abkühlen auf 20°C wurden 200 g Eiswasser zugetropft und die Mischung dreimal mit je 150 g Essigester extrahiert. Die vereinigten Extrakte wurden getrocknet und im Vakuum eingeengt.30 g of 2- (1-imidazolylmethyl) -N-phenyl-phthalimide were stirred in 60 g of monoethanolamine at 70 ° C. for 1 hour. After cooling to 20 ° C., 2 00 g of ice water were added dropwise and the mixture was extracted three times with 150 g of ethyl acetate each time. The combined extracts were dried and concentrated in vacuo.

Ausbeute: 13 g (75 % d. Th.) Fp. 42°CYield: 13 g (75% of theory), mp. 42 ° C

Beispiel 3Example 3 4,4;-Diamino-benzophenon4.4 ; -Diamino-benzophenone

20 g Bis-[4,4'-(Carboxi-phthalimidoyl)a-benzaphenon wurden in 30 g Monoethanolamin 15 Minuten bei 80°C gerührt. Anschließend wurden bei 20°C 200 g Eiswasser zugetropft. Der Niederschlag wurde abgesaugt, mit Wasser gewaschen und getrocknet.20 g of bis- [4,4 '- (carboxiphthalimidoyl) a-benzaphenone were stirred in 30 g of monoethanolamine at 80 ° C. for 15 minutes. 200 g of ice water were then added dropwise at 20 ° C. The precipitate was filtered off, washed with water and dried.

Ausbeute: 7 g (92 % d. Th.) Fp. 236°CYield: 7 g (92% of theory), mp. 236 ° C

Entsprechend den Beispielen 1 bis 3 wurden die folgenden Amine aus den Verbindungen der Formel I hergestellt:

Figure imgb0002
Figure imgb0003
Figure imgb0004
 The following amines were prepared from the compounds of the formula I in accordance with Examples 1 to 3:
Figure imgb0002
Figure imgb0003
Figure imgb0004

Analog zu den beschriebenen Methoden lassen sich auch die folgenden heterocyclischen Amine herstellen:

  • 2-Amino-4-phenylthiazol
  • 2-Amino-5-nitrothiazol
  • 2-Amino-3-cyan-4-methyl-5-aminocarbonyl-thiophen
  • 2-Amino-5-nitro-benzthiazol.
The following heterocyclic amines can also be prepared analogously to the methods described:
  • 2-amino-4-phenylthiazole
  • 2-amino-5-nitrothiazole
  • 2-amino-3-cyano-4-methyl-5-aminocarbonylthiophene
  • 2-amino-5-nitro-benzothiazole.

Claims (3)

1. Verfahren zur Spaltung von Phthalieiden der Formel I
Figure imgb0005
in der
R ein Substituent ist und der Ring A noch substituiert sein kann, dadurch aekennzeichnet, daß man die Verbindungen der Formel I mit Alkanolaminen behandelt.1. Process for the cleavage of phthalides of the formula I
Figure imgb0005
 in the
R is a substituent and the ring A can still be substituted, characterized in that the compounds of the formula I are treated with alkanolamines. 2. Verfahren gemäß Anspruch 1, dadurch gekennzeichnet, daß R ein aromatischer oder heteroaromatischer Rest ist.2. The method according to claim 1, characterized in that R is an aromatic or heteroaromatic radical. 3. Verfahren gemäß Anspruch 1, dadurch aekennzeichnet, daß man als Alkanolamin Monoethanolamin verwendet.3. The method according to claim 1, characterized in that monoethanolamine is used as the alkanolamine.
EP84105830A 1983-05-31 1984-05-22 Process for the cleavage of phthalimides Expired EP0127114B1 (en)

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DE3319650 1983-05-31
DE19833319650 DE3319650A1 (en) 1983-05-31 1983-05-31 METHOD FOR CLEAVING PHTHALIMIDES

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Publication number Priority date Publication date Assignee Title
DE3342462A1 (en) * 1983-11-24 1985-06-05 Basf Ag, 6700 Ludwigshafen METHOD FOR PRODUCING 4,4'-DIAMINOBENZOPHENONES
JP5036198B2 (en) * 2006-03-13 2012-09-26 エア・ウォーター株式会社 Phthalimides containing fluorene skeleton and diamines derived therefrom
DE112015005812B4 (en) 2014-12-25 2018-12-27 Ube Industries, Ltd. Process for the preparation of a nitrogen-containing pentafluorosulfanylbenzene compound

Citations (2)

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Publication number Priority date Publication date Assignee Title
DE2749415A1 (en) * 1977-11-04 1979-05-10 Bayer Ag METHOD FOR PRODUCING AMINES FROM FORMAMIDES
US4359584A (en) * 1979-09-22 1982-11-16 Basf Aktiengesellschaft Preparation of p-substituted, aromatic amines

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2749415A1 (en) * 1977-11-04 1979-05-10 Bayer Ag METHOD FOR PRODUCING AMINES FROM FORMAMIDES
US4359584A (en) * 1979-09-22 1982-11-16 Basf Aktiengesellschaft Preparation of p-substituted, aromatic amines

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, Band 50, Nr. 20, 25. Oktober 1956, Columbus, Ohio, USA N. RABJOHN et al. "Some reactions on N-acetylphtalimides" Spalte 14 644, Zusammenfassung-Nr. 14 645b, & J. Am. Chem. Soc. 78, 1631-4 (1956) *
CHEMICAL ABSTRACTS, Band 56, Nr. 1, 8. Janner 1962, Columbus, Ohio, USA KAZUO NAKAJIMA "Condensation reaction of amino alcohols with imides. I. Condensation products of N,N-diethylamino-ethanol with various imides; formation of N,N-diethyl-ethylene diamine" Spalte 404, Zusammenfassung-Nr. 405a, & Nippon kagaku Zasshi 81, 323-7 (1960) *
CHEMICAL ABSTRACTS, Band 60, Nr. 5, 2. Marz 1964, Columbus, Ohio, USA R. BORISAVLJEVIC et al. "N-Benzoylphtalimide. II. Reaction with amines" Spalte 5 390, Zusammenfassung-Nr. 5 390g, & Glasnic Khem. Drustva Beograd 27 (5-6), 299-311 (1963) *
CHEMICAL ABSTRACTS, Band 74, Nr. 7. 15. Februar 1971, Columbus, Ohio, USA S. WOLFE et al. "Five-membered rings. II. Inter- and intramolecular reactions of simple amines with N-substituted phtalimedes. Methylamine as a reagent for removal of a phthaloyl group from nitrogen" Seite 323, Zusammenfassung-Nr. 31 956y, & Can. J. Chem. 1970, 48(22), 3572-9 *
CHEMICAL ABSTRACTS, Band 90, Nr. 11. 12. Marz 1979, Columbus, Ohio, USA R. ALLEN et al. "Synthesis of some substituted 4-aminobut-2-enoic acids as analogs of the neurotransmitter GABA (a-amino-butyric acid)" Seite 665, Zusammenfassung-Nr. 87 858r, & Aust. J. Chem. 1978, 31(10), 2283-9 *
NATURE, Band 158, 1946, London H.J. BARKER et al. "Compositions of the antimalarial drug R. 63 and the Ing and Manske hydrazine hydrolysis of N-substituted phtalimides" Seite 514 *

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DE3319650A1 (en) 1984-12-06
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DE3461080D1 (en) 1986-12-04

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